Worst Generals, Commanders of Civil War

Confederate Maj. Gen. Gideon Pillow. After gaining ground trying to cut an escape path for the Confederates during the February 1862 siege of Fort Donelson by Union forces led Brig. Gen. Ulysses S. Grant, Pillow pulled the troops back to the fort to resupply them. As a result, he relinquished ground paid for with his soldiers' blood. Fearful of capture, he turned over command to Brig. Gen. Simon Bolivar Buckner and fled the fort on the night of February 16 in a boat that carried him across the Cumberland River to safety. For his cowardly performance, Pillow was severely reprimanded. Nevertheless, he commanded a brigade in Maj. Gen. John C. Breckinridge's Division at Stone's River, where once again he demonstrated his incompetence and cowardice.

Confederate Lt. Gen. Theophilus Holmes. Confederate General Robert E. Lee transferred several generals, one of whom was Holmes, out of the Army of Northern Virginia following the Seven Days Battles. Holmes had a talent for sitting on the sidelines and finding excuses not to attack, as he did at Malvern Hill. In his next post in the Trans-Mississippi Department, he failed to protect the Mississippi River outposts and refused to reinforce Vicksburg.

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